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He has everything a 32-year-old man could want. So why can't rock's biggest playboy shut up and enjoy it?

John Mayer goes out to a club, any club, he feels bad about it if some big host man makes someone get up from the banquette and take their Grey Goose elsewhere so the skinny rock star with the weirdly elevated hair can sit down. It doesn't exactly thrill him, either, when he's got to take a leak, and the line is long, and now the big man guarding the bathroom is making some dude hop on both feet so that Mr. Your Body Is a Wonderland can cut in and go first. It's embarrassing. But you know what he says is even worse? He sees a girl, any girl, and makes his move. He's a little tipsy. They end up in a room. Good things start happening. But then suddenly the girl's up on her feet and walking out.Mayer says this has happened to him more than once, so he knows what she's thinking: "Wait till I tell my friends I turned down John Mayer!" And it doesn't stop there. She turns to him, this girl he had longed for, however briefly, felt a connection with, felt hope. "Hey," she says, "before I go, can I have your autograph?"

Some time after the latest awful episode, he's downing a few Old-Fashioneds at a Los Angeles beautiful-people watering hole. Resplendent in a black-leather slant-zip jacket, obscure Japanese kicks and insanely expensive vintage Rolex, he's charging forward in his typical hyperbolic Mayerian way, saying stuff like "Blowing me off is the new sucking me off!" and "This is the death of rock & roll!" Suggest that maybe he's exaggerating, and he takes deep umbrage, jackknifing his long body forward. "No, man, and after that happens eight, nine times, I'd rather just go home and RedTube, good night. I'm serious."

And he looks serious, too. So maybe that really is his situation, despite who he is. Sure, lots of people don't like him and his music, too poppy, too sensitive, his head is too big, he uses the word "meta" too often. But his guitar chops, especially in the bluesy area, are unquestionably great, and he can count Eric Clapton among his admirers. Since 2001, he's released four studio albums, starting with Room for Squares, that have all been big successes, with hit songs like "Your Body Is a Wonderland," "Daughters" and "Waiting on the World to Change." And while his newest record, Battle Studies, isn't up to his previous one, Continuum (an assessment even Mayer agrees with: "I know that I'm supposed to say that my newest is the best one. Bullshit. Continuum is my best one. And I think you gain more than you lose by saying that"), it debuted at Number One. In fact, commercially, Mayer has never come close to failing. He's a golden boy (whose label, Columbia, had the good sense to sign him to a 10-year Fort Knox-size deal in 2008).

Meanwhile, for better or worse, he's become a kind of inescapable pop-culture staple. He's huge on Twitter, where he is an acknowledged modern-day master of the lowbrow bon mot, having amassed a fan base of 2,919,691 souls who hang on his every "My mouth is the Don King of my penis" and "I thought I had to fart but it turned out it was just a poop." He's everywhere in the gossip press, often in connection with celebrity ex-girlfriends, the last being Jennifer Aniston, who followed Minka Kelly, who followed Jessica Simpson, etc. And every time he sees a paparazzi, he can't help himself, he's got to act out; just the other day, he and his friend the well-known lesbian Samantha Ronson engaged in a bit of hot up-against-the-wall-oral-sex silliness for the cameras. Really good stuff.

But here he sits tonight, leather jacket pulled in tight against an early-evening chill, big soulful puppy-dog eyes looking more pensive than usual. Momentarily, he stands up to try to get a propane porch heater started. It frustrates him. He clicks away, no luck, turns, sits down, gets up, tries once more, no luck, gets someone else to do it, eyeballs some girls at a nearby table, says nothing to them ("When it's time, my mouth will just start going"), returns to his drink. Soon enough, he starts in on that one area of his life that he is most consumed by and least happy with.

He thinks about it constantly. He talks about it endlessly. He wants a girlfriend, a real life-partner girlfriend. It's been a long time. And it's just not happening.

"All I want to do now is fuck the girls I've already fucked, because I can't fathom explaining myself to somebody who can't believe I'd be interested in them, and they're going, 'But you're John Mayer!' So I'm going backwards to move forward. I'm too freaked out to meet anybody else."

He puts down his drink.

"What do you think?" he says. "Do you think it's going to take meeting someone who I admire more than I admire myself? But isn't it also about a beautiful vagina? Aren't we talking about a matrix of a couple of different things here? Like, you need to have them be able to go toe-to-toe with you intellectually. But don't they also have to have a vagina you could pitch a tent on and just camp out on for, like, a weekend? Doesn't that have to be there, too? The Joshua Tree of vaginas?"

And so the search continues. He knows she is out there. And he will not stop until he finds her, and her Joshua Tree of vaginas.

It's 4 a.m. at his place in Calabasas, 30 miles northwest of L.A., which he rented to record Battle Studies in. On any given night, he's still awake. He's maybe watched a little 30 Rock, South Park or Family Guy, his favorite TV shows. He's smoked a little weed, gotten a nice little buzz working, hit the send button on a few Twitters and lost himself in Modern Warfare 2. All cozy in sweatpants and a hoodie, he usually turns in now; if he hasn't by 7 a.m., it's time for a Xanax or an Ambien. When he gets up, usually around noon, he drinks some coffee, eats breakfast, brushes his teeth, hits the shower and stands in front of a great big closet (he spent about $200,000 on clothes last year) asking himself one of life's more important questions: "Who the fuck do I want to be today?"

His choices, he says, generally boil down to "urban technical, Japanese schoolboy, white Jay-Z or skinny, sleek rock guy." He hasn't done Japanese schoolboy in a while but today slips into skinny, sleek rock guy, in black cargo pants and a pair of white Mastermind sneakers. As the day wears on, he might call his shrink, which he does on "an as-needed basis." He might practice the Israeli fighting art of Krav Maga, which he got totally into after breaking up with a girl and deciding to "get good at something she doesn't know about." He might call his friend Bob, a fellow vintage-watch nut, to discuss their collections. Mayer's is worth at least $20 million; he can recite his holdings by heart; he knows all the numbers; he once stumbled across a rare Rolex dial variant, which is now known as "the Mayer dial." An obsessive, he has also collected sneakers, ladies' handbags, cameras, lots of stuff. He owns a bulletproof vest — "I looked up California penal code 12022.2, subsection B. In this state, I'm legally allowed to wear it" – and wants to own an M4A1 assault rifle, "just to go, 'Look what I have that no one else has.'" He once got magician David Blaine to teach him how to hold his breath and then did so for four minutes, 17 seconds, no tricks involved, which says a lot about the kind of guy he is: tenacious, nutty and blue-in-the-face sometimes.

Later on, in a restaurant or club, he will have to take a leak and head straight for a stall. ("I've got to go to the stall. I can't get a good flow going when I'm out in the world. But then, of course, you run the risk of people thinking you shit all the time." He endures.) In the evening, he favors single-malt Lagavulin scotch (and drinks about a bottle of it a week), but only in L. A. In New York, where he owns a home, he doesn't drink that much. It has to do with the hangover. "On the West Coast in the morning, it's like Bob Dylan with a coffee; on the East Coast, it's socialites getting penicillin shots," he says obliquely. "I can't drink in New York."

Along the way, he tries to explain himself and his various predilections. His love of poop Twitters, for instance. "I mean, in the wake of some completely fabricated story in Star, you'd be surprised what a good poop joke can do for you. When I send a poop joke out on Twitter, every single time, people write back, 'LOL, that's why I love you. You're not like every other bullshit celebrity.' It shows an artist detaching from the matrix of trying to micromanage per-fection. It's about not caring. So, it's not really about poop at all."

This is pure Mayer talk. Nothing is what it seems. He operates in layers of meaning, where a poop joke is so much more than a poop joke. "He's a student of cause and effect," says Chad Franscoviak, Mayer's sound engineer and sometime roommate for the past 10 years. "And he'd be a phenomenal chess player, because he knows all the moves so many steps ahead. That's just how he operates."

"I am the new generation of masturbator," Mayer says later on, out of the blue, apropos of nothing, really. "I've seen it all. Before I make coffee, I've seen more butt holes than a proctologist does in a week."

Does this new generation of masturbator masturbate every day?

"I don't like that question, because it seeks to make me sound strange if I say 'yes,' but of course I do. I mean, I have masturbated myself out of serious problems in my life. The phone doesn't pick up because I'm masturbating. And I have excused myself at the oddest times so as to not make mistakes. If Tiger Woods only knew when to jerk off. It has a true market value, like gold bullion. First of all, I don't jerk off because I'm horny. I'm sort of half-chick. It's like District 9 – I can fire alien weapons. I can insert a tampon. No, I do it because I want to take a brain bath. It's like a hot whirlpool for my brain, in a brain space that is 100 percent agreeable with itself."

After that, he continues in like manner, revealing another one of his situations. He's in love with the sound of his own voice, always saying things like, "Let me break it down for you," and then laying into it with revelatory verbal fireworks of the kind that constantly threaten to blow him to smithereens. He can't help himself, he's got to say what's on his mind, despite the consequences, which often get played out in the tabloids and on trash TV, such as the time during a stand-up-comedy gig when he said he never got to have sex with early girlfriend Jennifer Love Hewitt because of a bout of food poisoning.

"I sometimes wonder what the fuck I'm doing," he says. "I have these accidents, these mistakes, these self-inflicted wounds, and then I tear my head to shreds about it for days. I'll read a little something and die a thousand times in my own mind, visualizing the death of my career or respect for me and my music. I almost go blind. But then two weeks ago, it occurred to me, 'John' – if I can use my own name with myself – 'The only reason you're going through these trials is because you're brave-enough to say, "I don't want to detach. I don't want to go live in a gated community."' So, I will continue to make these worldwide dignity mistakes as often as it takes to not make them anymore."

How Mayer got to be like this is kind of a mystery. He grew up in the leafy Connecticut town of Fairfield, the middle son of level-headed professional educators. His mom, Margaret, was an English teacher; his dad, Richard, some 20 years his mom's senior, was a high school principal, and Mayer wasn't anything like them. A class clown in his early years, Mayer had taken up the guitar by his midteens and had begun shutting himself off in his room to the exclusion of everything else. It's all he did and all he wanted to do — "kill it, kill it, kill it," with that guitar. He plastered his room with posters of Stevie Ray Vaughan, B.B. King, Jimi Hendrix. While the other kids were listening to Nirvana, Mayer was deep into reading the Buddy Guy biography Damn Right, I've Got the Blues and cutting out the photos when he was done.

"He kept to himself quite a bit back then, and he was pretty quiet in school but hilarious once we got outside," says Fairfield-raised tennis pro James Blake, who's known Mayer since they were seven. "He seemed pretty disinterested in what was going on in school."

For several years, Mayer took guitar lessons from Al Ferrante, owner of the Fairfield Guitar Center. "He came in holding a Stevie Ray Vaughan album, said, 'I want to learn this stuff,' and in short order he was wailing away," says Ferrante, "way beyond anybody else." To his friends,Mayer's talent was obvious. "He could play the guitar and drum at the same time," recalls Joe Beleznay, who played rhythm guitar in Mayer'shigh school band, Villanova Junction (named after the Hendrix song). "He'd sit behind the drum set, get the bass drum going, then on the down strum of his guitar he'd hit the snare. It was crazy, inventive shit. He just had it." Says Blake, "With girls, I wouldn't say he had the same kind of success he's had now, but he didn't put in the same kind of effort. His focus was on that guitar." At some point, however, this single-minded devotion to music so freaked his parents out that they sent him to shrinks to see if something was wrong (he was given a clean bill of health). Meanwhile, the kid had his own worries. For one, his parents fought a lot, which he says led him to "disappear and create my own world I could believe in." Also, he'd begun to suffer from anxiety attacks and feared ending up in a mental institution. "Growing up," Mayer says, "that was the big fear." Says his pal Beleznay, "I would get anxiety attacks too, and we would talk each other down. It was heart palpitations, shortness of breath, coldness and shivers, strange stuff, and we'd be like, 'You're totally fine. You're not having a heart attack.' His mind works at such speed that I think he would sort of second-guess his sanity at times."

In his senior year, Mayer decided he was going to skip traditional higher education and become a musician. "I tried to talk him out of it," says Blake, "but then he told me that he didn't care if he was sleeping on a pool table in a dirty bar, he just wanted to play music." When he told his parents the same thing, all hell broke loose. Their reaction was so strong that even today Mayer wraps himself up in his arms while talking about them and says, "Look at my body language. My goodness."

After graduation, he attended Berklee College of Music in Boston — while there, his father had a change of heart and sent "him a note that read, 'Remember me when you go platinum'" — but Mayer dropped out after a year and moved to Atlanta, to join its thriving singer-songwriter scene. He started off playing Monday's open-mike night upstairs at Eddie's Attic and soon became a regular performer there, as well as a part-time doorman. "He was very talented and extremely determined — as determined as anybody I've ever met," recalls Eddie's Attic founder Eddie Owen. "He thought it was going to happen for him, and by God he did everything he could to make it happen."

Even so, he could still be a shut-in. He had terrible acne and often canceled dates because of it. Eventually, he suffered a kind of breakdown — "an anxiety bender," he once called it — out of which came a new Mayer, the freewheeling social-animal Mayer, the Mayer we know today. In 2000, a gig at the South by Southwest music festival in Austin led to meetings with several record labels, during which he behaved in typical strong-willed Mayerian fashion.

"As a kid, he picks up a guitar and isolates himself because he's so overtaken by passion for the instrument or because he's not comfortable socially and is an outsider," says Michael McDonald, his manager and friend for the past 10 years. "And then at home, his pursuit isn't supported. But what happened was he became his own biggest advocate. When he went to those meetings, he would tell people how he wanted it to be, and if they offered alternatives, he walked away."

Eventually, Mayer signed with Aware/ Columbia. Shortly thereafter, Room for Squares was released, "Your Body Is a Wonderland" became a hit, as did "Daughters," from his second album, Heavier Things, and everyone was happy, especially the label, which was hotly anticipating a third record full of similar radio-ready tunes. Instead, in 2005, Mayer presented it with the cool blues of the John Mayer Trio. Says McDonald, "They were like, 'Oh, fuck. Can we please make it an EP?' But John's got a course charted that he doesn't share, and the Trio, to him, was an answer to 'Wonderland' and 'Daughters' — not a rebellion against but an answer to."

The Trio's live record, Try!, didn't do as well as Mayer's other albums, but that was hardly the point. The point is, he will showcase his talents on his own schedule.

And so forward he moves, on a journey that seems to have gone by with wondrous ease, except, of course, for the acne, and the shut-in business, and the worries about a mental institution, and the anxiety bender — all of which, sum in toto, are probably responsible for the way he is today, this willy-nilly scattered metaminded eccentric who seems next-door normal only on his records. He recently told MTV, "You get kicked in the heart by someone who's aware of it or not, and you get sent alone into a room, and if you have a little bit of intellect, a little bit of talent and a lot of loneliness, you'll probably make it."

Now that Mayer has left the cloistered seclusion of his room, however, what he seems to want more than anything is to make up for his loneliness by courting mass attention. It's what his public life is about. It's why he decided to make records like Battle Studies that back-seat his scorching blues guitar in favor of pop-happy lyrics and commercial melodies, the Trio album notwithstanding, and why he even sings songs at all. As far back as 2002, he was saying things like "I scientifically engineer my music to be as accessible as possible," just as today he says, "I love being a famous musician. I love being the center of attention. I believe in judging the quality of a song by how much of a hit it sounds like." At least he's honest. But the ultimate effect is to make Mayer the singer-songwriter and Mayer the man about town sometimes seem disconnected, like they don't even belong in the same body. He says he's going to shake things up on his next record. "I want the next one to be gritty, real gritty," he says. "The no-ballad gritty one." But then he laughs and says, "One ballad." And then he laughs again and says, "I've got a built-in failure attenuator." He gives, he takes away, he's got his course charted, he's a blues killer, he's a pop superstar, he seems so open, he seems so shut, he is a master of disguise.

Last year, his folks finally got divorced, after which Mayer moved his dad, now 82 years old, out to California, to an independent-living facility, where he could see him more often and help take care of him. Mayer won't talk about it, though, what it means to be so close to his father at this stage of his dad's life. Nor will he let you talk to his dad, or his mom, or his brothers, like they might reveal some strange truth. In fact,Mayer is cagey about his Fairfield years. He can talk about the most intimate details of his personal life, but about his childhood, and the forces that shaped him, he remains steadfastly mum. But maybe that's the way it should be. Perhaps it's best to rise above the gnawing tabloidlike need to have all mysteries revealed.

Mayer does say that ever since the divorce, he has felt slightly adrift. "I was in L.A., making the record, when it happened. You get orphaned. I never went home. I never went back to the home I grew up in. I never went and saw it again. It happened. My house is gone." Among other things, it's the house where, at the age of 14, he fell in love with the girl who would inspire "Your Body Is a Wonderland" and without whom he would not be where he is today. He recently got an e-mail from her. "It was a beautiful e-mail about what it's like to hear me on the radio," he says. "She said she smiled. I started crying as I wrote her back. This woman is precious. She can vouch for me not as a celebrity. She carries with her information of this 14-year-old boy she knew. She knows the truth. She hadn't written me in a long time. I think she was trying to forget me because she has a husband and kids." That's one possibility. But there's another possibility: that Mayer is the one who continues to pine, either for her or the idea of her and their shared innocence, his pre-celebrity existence, and he can't bring himself to say so.

Over the year, lots of musicians have weighed in on Mayer's talents. Said Fall Out Boy's Patrick Stump, "Mayer is single-handedly making the Stratocaster cool again!" Said Buddy Guy," Every once in a while, a young man comes along to make sure the blues can survive." Said a puzzled Ozzy Osbourne, " 'Continuum: Music by John Mayer,' whoever that is. 'Continuum.' I couldn't understand what that word meant." Said Jason Mraz, after seeing Mayer kill at the Viper Room, "He didn't play no 'Body Is a Wonderland.' He was playing for his love of music. He was Jimi Hendrix and Buddy Guy and Stevie Vaughan all rolled up into one big reincarnation burrito."

In 2006, Mayer spent 10 days working on songs with Eric Clapton at Clapton's estate, where Mayer seemed to have reverted to some of his childhood ways. "He treated our days together as work," says Clapton, "and I tried to point out to him the importance of music being the truth — and to get him to come out of the bedroom. There are a lot of bedroom guitar players. And John was in and out of that. I wasn't sure ifJohn was aware of the power of playing with other people, though I think he is now." He goes on, "I think he becomes too caught up in being clever. It seems to me his gift happens in spite of him. He's a prime saboteur. And he will do himself in, if everyone lets him. But his gift is in good shape."

And while all of that is very interesting, it's not really what people reading tabloids care about. All they care about is "Who is Mayer going out with now?"

Jessica Simpson was his first big tabloid-heavy romance. They got together in mid-2006 and went public at Christina Aguilera's New Year's Eve party and then they got swarmed. At first Mayer didn't think he could handle all the media heat — "I got so many tension headaches from magazine covers that it felt like a threat" — but stuck it out with her for just shy of a year. Then there's his latest, Jennifer Aniston, and it was the purest kind of celebrity relationship, almost every minute of it documented in one way or another. When it ended, Mayer held an impromptu press conference outside his New York gym in which he planned to flay himself alive for breaking up with Aniston — "I'm the asshole. I burned the American flag. I basically murdered an ideal." Instead, he came off like a jerk only interested in taking credit for the breakup. "I've never really gotten over it," he says. "It was one of the worst times of my life."

He still thinks about Aniston a lot, and in conversation her name pops up often.

"I met a girl one time in Vegas, her name was Dimples, and the 'S' in Dimples was a dollar sign," he's saying early one evening sitting outside at the Chateau Marmont hotel. "I have this weird feeling, a pride thing, for the people I've had relationships with. I still feel like I'm with them, in the sense that if I fucked Dimples, what does that say about someone like Jen? I feel like it's all connected. How could I ever cosmically relate these two people? What would I be saying to Jen, who I think is fucking fantastic, if I said to her, 'I don't dislike you. In fact, I like you extremely well. But I have to back out of this because it doesn't arc over the horizon. This is not where I see myself for the rest of my life, this is not my ideal destiny,' and then I see myself fucking Dimples? What does that say for my case?"

Then again, there is what he did last summer. At a hotel in Vegas, he saw some girls by the pool, one thing led to another, and they all wound up in bed together. "And you know what? It wasn't smarmy. It was awesome. And then, after that, when I went out that night, I had the greatest time ever, because I was depleted, had no libido left, didn't have to do any of those crazy Blue Steel looks. It was unbelievable."

A waiter shows up. Mayer orders chicken. But then he realizes he ate chicken yesterday. "Fuck the chicken," he says and calls out for spaghetti Bolognese.

"I'll be honest with you," he says then. "All this weird shit about me? All this strangeness? I wouldn't have a music career without it. But I am at odds with myself. I have some presence of psychological damage from the past 36 months. I have not had a woman appear in my dreams sexually without a paparazzi in the dream too. I can't even have a wet dream without having to explain to someone who's grinding on me, 'We can't do this right now, because there's a guy over there taking pictures.'" He groans. "I don't know how much further I can do this before I'm a dead body on the side of the road. I mean, either I'm a total fucking nut case who can explain himself, or I'm really not crazy and I can explain myself. I don't know yet. But I'll be happy when I close out this life-partner thing. It's been a long time since I've felt attached. Think of how much mental capacity I'm using to meet the right person so I can stop giving a fuck about it."

He's on a real roll right now, caught up again in the workings of his own mind. At times like these, it's impossible to get a word in edgewise. It seems dangerous to even try. It's best just to let him go on, reserve judgment, realize that, above all else, he means well and is simply, in the end, only trying to find his way, as best he can.

"I don't care about anything other than energy," he goes on. "That's why people think, 'Is he bi? Is he that?' I've never slept with a man. But I get it. I've seen pictures of men on the Internet that are sexier than pictures of most women."

Has he ever felt it stir?

"Sure. Abso-fucking-lutely. You know when I didn't feel it stir? When I actually stood next to a real dude. When I walk in the locker room at the gym, I'm 100 percent straight as an arrow. But, look, because of all the porn I've watched, I'm now enamored with what I call 'the third kind.' It's not male, it's not female. It's a new creation by way of the hundreds of blow-job films I've seen. There's a new brand of dicks going around right now. It's a new dick. It's a superdick. This superdick is straight and one color, and it seeks to destroy the race of men before them.

"I have a hugely creative and visual relationship with things," he continues. "So what's my job going to be? Finding somebody to be the only person. Basically, what am I going to do with my imaginary headless, hung dudes without a hair on them or anything masculine about them? What am I going to do with those dicks when it comes time to find somebody? Do they go away? Do you find a woman who incorporates it? Do you love this woman so much you no longer need it? I'm like in Avatar. I'm a legless, dickless dude laying in a chamber, projecting myself in all ways. I'm this legless asshole — "

A few cute girls walk by. Mayer finally stops talking. He looks at them but that's all. "If I talk to them, I'm expressing an interest I'd be betraying if I saw someone else that I wanted to talk to more. It's too early in the evening, and they'd be a sidecar. Anyway, here's how tonight's going to go. After this, I'm going to go home, smoke weed, and play Modern Warfare 2. It's what I'm going to do all night." But then he tilts his nose into the air, says he's good with scents and would bet money that one of the girls is wearing a perfume called Child. "If you're wrong, you're an idiot. If you're right, you're like James Bond."

He turns to them. "Excuse me, can I be rude and ask you a question? Is somebody here wearing Child?"